If there's a maelstrom in Connecticut politics, chances are Tim Herbst is in the middle of it.

Turmoil follows Trumbull's first selectman wherever he goes, leaving a trail of bruised egos, lawsuits and a growing list of enemies.

The latest: A border war with Bridgeport over a Herbst-led withdrawal of the regional planning council from the state's largest city. The snub has placed further strain on Herbst's already tenuous relationship with next door Mayor Bill Finch.

On the home front, Herbst is mired in a perpetual struggle with Democrats over town affairs, from his leadership style and personnel moves to contracting and litigation. The 34-year-old makes no bones about his aggressive approach, which, he points out, hasn't stopped Trumbull voters from electing him three times.

"I don't pull any punches," Herbst said. "Look, the older I get the less I care about what people think about me."

The list of people Herbst has rankled during his six years in office cuts across party lines. It ranges from the state's former top Democrat, fellow Trumbullite Nancy DiNardo, to the state's top Republican, Jerry Labriola Jr. Herbst called for Labriola's resignation last fall following the GOP's dismal election results, when Herbst ran a competitive but unsuccessful race for state treasurer.

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And now Finch, who said last week in an interview that he's tired of people like Herbst knocking around his city.

"I would say it's a relationship that needs a lot of tending to," Finch said. "I think he might be a little brusque from time to time. I'm sure I am, too, from time to time. We're going to bump heads once in a while."

Finch was referring to an April 2 confrontation with Herbst during a meeting of the Greater Bridgeport Regional Council, which Herbst, as the group's chairman, wants to move outside the city limits because of security concerns.

"I was certainly blind-sided by an extreme action," Finch said. "I have a lot of pride in my city and I'm always going to bang my hand on the table for my city. If you don't like it, then too damn bad."

For his part, Herbst referred to Finch publicly as a bully with anger management issues.

After the two sides could not come together, the General Assembly stepped in and annnexed 48 acres of Trumbull to Bridgeport, where the school is located. Herbst then accused Finch of reneging on the transfer of 20 acres for a greenway.

"There are certain things that you don't forget that you file," Herbst said. "I'm from the old school. In politics, you're only as good as your word. Those are the kind of things that you keep in the back of your mind and remember in any future dealings."

Critics say no one holds a grudge like Herbst. They say his Nixonian paranoia and habit of dredging up dirt on opponents often scare people away from challenging him in the political arena.

"Tim is pretty much a lightning rod," said Tom Kelly, Trumbull's Democratic Town Committee chairman. "I don't think every issue needs to be handled with a sharp tongue or a heavy hand."

"People are just so controversy-averse and that's just not him," said Liz Kurantowicz, a former chief of staff for the Connecticut GOP who volunteered on Herbst's treasurer campaign. "He's not afraid to get his hands dirty."

Herbst's tenacity has sometimes served the town well. His frequent calls for audits of town departments have exposed wasteful spending and cost overruns from snow removal, sewer projects and the renovation of Trumbull High School. It's that bottom-line mentality that Republicans credit for Herbst's success at the ballot box, where he got 70 percent of the vote in 2013. Herbst, who is single and is juggling law school and mortgage payments, is seeking re-election this year.

"A lot of people, maybe jealousy might be the right word, feel he might be too aggressive," Testani said. "Because it's common sense and brass tacks, so to speak, a lot of people take that as being brash."

No Republican running for statewide office performed better than Herbst in the November election, when he garnered 49 percent of the vote but lost to Democratic incumbent Denise Nappier.

Since then, Herbst has flexed his muscles in the GOP, pushing for Labriola's removal as party boss and replacement by J.R. Romano, a college buddy who managed Herbst's treasurer campaign.

To some in the GOP, the no-confidence measure was seen as a power play for the next statewide election in 2018 and potential run for governor by Herbst.

"Tim is at his best challenging Democrats while collaborating with all Republicans," said Edward Dadakis, a Herbst mentor and Republican State Central Committee member from Greenwich. "Tim is really an outstanding young Republican leader. Tim calls it the way it is. And he's almost always right. It can be controversial at times."

Labriola declined to comment. His term expires in June.

Romano, of Derby, a former political director for the state GOP, said Herbst only wants what's best for the party.

"Tim recognizes that we need to fundamentally change how we're operating as a party," Romano said. "What our state party needs is a tactician."

Likes to win

Democrats say no one is more political than Herbst and pointed to his social media attacks, like when Democratic Gov. Dannel P. Malloy visited Trumbull earlier this month for a Democratic town fundraiser. The next day on his Facebook page, Herbst wrote, "Last night, the most unpopular governor in the United States, `Angry' Dan Malloy came to town to say `Trumbull can do better.'"

"The kid spends more time on Facebook than he does in his office," said Al Barbarotta, a Trumbull construction manager and friend of Malloy's. "He just attacks like he's always campaigning to be the next governor. He trusts no one. He's mean, he's arrogant and he's a despot."

Herbst said Barbarotta has no moral high ground and even used his friendship with the governor to promote his energy business to Newtown officials after the Sandy Hook Elementary School shooting.

"I personally have no respect for that man or anything he has to say," Herbst said. "How he sleeps at night and shows his face is beyond me. The fact the governor associates with a person like that says more about the governor than it says about Mr. Barbarotta. You can tell the governor I said that, too."

Malloy's office declined to comment. So did DiNardo, who was chairwoman of the Connecticut Democrats and the Trumbull DTC at the same time for several years.

"She's a worthy adversary and I have a great deal of respect for her," Herbst said of his rival. "But I do like beating her."